Nitric Acid → Methyl 5-methoxy-4-(2-methoxyethoxy)-2-nitrobenzoate

HRID 1917638Notes

Reaction equation

HRID 1917638 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][O:16][CH3:17])[C:6]([O:8][CH3:9])=[O:7].[N+:18]([O-])([OH:20])=[O:19]>CC(O)=O>[CH3:1][O:2][C:3]1[C:12]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[CH:11][C:10]([N+:18]([O-:20])=[O:19])=[C:5]([CH:4]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 60351193Methyl 3-methoxy-4-(2-methoxyethoxy)benzoate

Product 1

HCID 66876504Methyl 5-methoxy-4-(2-methoxyethoxy)-2-nitrobenzoateYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Using the procedure described in Example 6A Step 2, methyl 3-methoxy-4-(2-methoxyethoxy)benzoate (8.39 g, 34.9 mmol) was reacted with fuming nitric acid (90%, 3.15 g) in AcOH (60 mL) at 50° C. for 8 hours, to afford methyl 5-methoxy-4-(2-methoxyethoxy)-2-nitrobenzoate as a yellow solid (7.956 g, 80%). 1H NMR (300 MHz, CDCl3) δ 7.51 (s, 1H), 7.07 (s, 1H), 4.25 (t, 2H), 3.96 (s, 3H), 3.91 (s, 3H), 3.82 (t, 2H), 3.46 (s, 3H); LC-MS (ESI) m/z 286 (M+H)+.

Sources & evidence

ORD record
ord-6f0ec24fe9fd451faaf7f97963853066
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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